Acetonitrile → HCID 117622767, compound

HRID 56879Notes

Reaction equation

HRID 56879 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([C:29]#[N:30])=[C:6]([C:8]2[C:13]([O:14][CH3:15])=[CH:12][N:11]([CH:16]([CH2:20][C:21]3([C:24]([F:27])([F:26])[F:25])[CH2:23][CH2:22]3)[C:17](O)=[O:18])[C:10](=[O:28])[CH:9]=2)[CH:7]=1.[NH2:31][C:32]1[CH:44]=[CH:43][C:35]([C:36]([O:38][C:39]([CH3:42])([CH3:41])[CH3:40])=[O:37])=[CH:34][CH:33]=1.CC(C)N=C=NC(C)C.C(#N)C>CN(C)C=O>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([C:29]#[N:30])=[C:6]([C:8]2[C:13]([O:14][CH3:15])=[CH:12][N:11]([CH:16]([CH2:20][C:21]3([C:24]([F:26])([F:27])[F:25])[CH2:22][CH2:23]3)[C:17]([NH:31][C:32]3[CH:44]=[CH:43][C:35]([C:36]([O:38][C:39]([CH3:40])([CH3:41])[CH3:42])=[O:37])=[CH:34][CH:33]=3)=[O:18])[C:10](=[O:28])[CH:9]=2)[CH:7]=1

Participants

6

Reactant 4

HCID 6342Acetonitrile4×HCID 12734DiisopropylcarbodiimideHCID 233272Benzoic acid, 4-amino-, 1,1-dimethylethyl esterHCID 117622868HCID 117622868, compound

Product 1

HCID 117622767HCID 117622767, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

188 mg (426 μmol) of 2-[4-(5-chloro-2-cyanophenyl)-5-methoxy-2-oxopyridin-1(2H)-yl]-3-[1-(trifluoromethyl)cyclopropyl]propanoic acid (racemate), 82.4 mg (426 μmol) of tert-butyl 4-aminobenzoate, 6.1 mg (43 μmol) of Oxima and 66 μl (0.43 mmol) of DIC in 4 ml of dimethylformamide were reacted according to General Method 5B. Following preparative HPLC [column: Chromatorex C18, 10 μm, 125 mm×30 mm, mobile phase: acetonitrile/0.1% formic acid gradient (0 to 3 min 10% acetonitrile, to 35 min 90% acetonitrile and a further 3 min 90% acetonitrile)], the title compound was obtained. Yield: 157 mg (59% of theory)

Sources & evidence

ORD record
ord-4a47032ba20b41afb36df60ceea71932
Source dataset
uspto-grants-2016_09
Patent number
US09434690B2

Reaction notes

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